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Fmoc-Compatible and External-Thiol-Free Peptide C-Terminus Alkyl Thioester Formation Using Cysteinylprolyl Imide

29 April 2020, Version 1
Working Paper
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

We report an Fmoc-compatible and external-thiol-free method of peptide C-terminus thioesterification with cysteinylprolyl imide. The newly synthesized structure, i.e., cysteinylprolyl-thiazolidinone, provided high conversion and sequence-independent fast kinetics (90 min) in the diketopiperazine thioester formation under relatively mild conditions: pH 6.0, 37 °C. Employing this thioesterification method, we synthesized histone H3.2 bearing K56 acetylation.

Keywords

Peptide Thioesters

Supplementary materials

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Title
SI Fmoc-compatible and External-thiol-free Peptide C-terminus Alkyl-thioester Formation Using Cysteinylprolyl Imide (CPI) okamoto2
Description
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Version History

Apr 29, 2020 Version 1

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The content is available under CC BY NC ND 4.0 [opens in a new tab]

DOI

10.26434/chemrxiv.12154722.v1
D O I: 10.26434/chemrxiv.12154722.v1 [opens in a new tab]

Author’s competing interest statement

None

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